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How can I determine if I'm ready to join a startup as one of the first few engineers?

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Anonymous User at Taro Communitya year ago

I've worked as a software engineer at startups with 20-400 people as well as a large public company, and have especially enjoyed working in a startup environment and am interested in becoming an entrepreneur and maybe starting my own company one day. To learn more about what it's like in the very early days of starting a company and finding product-market fit, I'm currently exploring opportunities at seed-stage startups with less than 10 people where I would be one of the first few engineers in the company and the lead frontend engineer initially building the entire frontend from scratch for the company's MVP. I have three years of experience as a frontend engineer and have recently been serving as a technical lead on my team at a late-stage startup. I've also helped build out the frontend for an MVP at a startup before, but as one of a few engineers working on the frontend, not as a solo lead frontend engineer yet.

Would appreciate any advice on a few questions I'm thinking through:

  1. Aside from evaluating the promise and culture fit of a company itself, what are factors to consider when deciding whether being one of the first few engineers at a seed-stage startup is the right fit, especially if I'd be the lead or only engineer owning a significant part of the product delivery e.g. building the entire frontend for an MVP? How do I figure out if I'm ready for this level of responsibility?
  2. As the only engineer at a company with expertise in a particular domain (e.g. frontend), when you inevitably get stuck at some point despite trying a lot and reading a lot of stackoverflow etc., who do you turn to or how do you work through it if there are no other engineers at your company yet who can help meaningfully since they aren't very familiar with your domain?
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    Senior Software Engineer at IBM
    a year ago
    1. I'd be asking how comfortable do you feel with the technology? Can you eat, breathe, and sleep it? Can you come up with creative ideas on the fly where others are like "Oh wow, they're really smart"? Could I put you in situations with absolutely no design whatsoever and have you come up with a prototype architecture we can scale to production usage? It sounds like you're already on your way there, but I recommend finding one who casts a vision you really feel inspired by and would love to have on your resume.
    2. Luckily there's help to that at each stage in the process and it really depends on where your funding comes from. Incubators and accelerators can be incredibly helpful regardless and pair you up with a good amount of people in the short term to learn a good amount. Shortening the workday when particularly stuck and deep-diving on a topic could really help blow the doors open on an otherwise hard to achieve problem. At any stage of the process too, any founder should have a good amount of funding sitting around with a plan to scale up the business. If you continually get stuck, it could mean it is time to go and ask for help in scaling the business.